diff --git a/src/node_contextify.cc b/src/node_contextify.cc
index c4db3eb076d49b..bc3447109b900e 100644
--- a/src/node_contextify.cc
+++ b/src/node_contextify.cc
@@ -1647,6 +1647,12 @@ static const auto throws_only_in_cjs_error_messages =
         "await is only valid in async functions and "
         "the top level bodies of modules"};
 
+static const auto maybe_top_level_await_errors =
+    std::array<std::string_view, 2>{
+        "missing ) after argument list",  // example: `func(await 1);`
+        "SyntaxError: Unexpected"         // example: `if(await 1)`
+    };
+
 // If cached_data is provided, it would be used for the compilation and
 // the on-disk compilation cache from NODE_COMPILE_CACHE (if configured)
 // would be ignored.
@@ -1877,6 +1883,16 @@ bool ShouldRetryAsESM(Realm* realm,
       break;
     }
   }
+
+  for (const auto& error_message : maybe_top_level_await_errors) {
+    if (message_view.find(error_message) != std::string_view::npos) {
+      // If the error message is related to top-level await, we can try to
+      // compile it as ESM.
+      maybe_valid_in_esm = true;
+      break;
+    }
+  }
+
   if (!maybe_valid_in_esm) {
     return false;
   }
diff --git a/test/es-module/test-esm-tla-syntax-errors-not-recognized-as-tla-error.mjs b/test/es-module/test-esm-tla-syntax-errors-not-recognized-as-tla-error.mjs
new file mode 100644
index 00000000000000..a9dc6785c45ecd
--- /dev/null
+++ b/test/es-module/test-esm-tla-syntax-errors-not-recognized-as-tla-error.mjs
@@ -0,0 +1,77 @@
+import { spawnPromisified } from '../common/index.mjs';
+import { describe, it } from 'node:test';
+import { strictEqual, match } from 'node:assert';
+
+describe('maybe top-level await syntax errors that are not recognized as top-level await errors', () => {
+  const expressions = [
+    // string
+    { expression: '""' },
+    // number
+    { expression: '0' },
+    // boolean
+    { expression: 'true' },
+    // null
+    { expression: 'null' },
+    // undefined
+    { expression: 'undefined' },
+    // object
+    { expression: '{}' },
+    // array
+    { expression: '[]' },
+    // new
+    { expression: 'new Date()' },
+    // identifier
+    { initialize: 'const a = 2;', expression: 'a' },
+  ];
+  it('should not crash the process', async () => {
+    for (const { expression, initialize } of expressions) {
+      const wrapperExpressions = [
+        `function callAwait() {}; callAwait(await ${expression});`,
+        `if (await ${expression}) {}`,
+        `{ key: await ${expression} }`,
+        `[await ${expression}]`,
+        `(await ${expression})`,
+      ];
+      for (const wrapperExpression of wrapperExpressions) {
+        const { code, signal, stdout, stderr } = await spawnPromisified(process.execPath, [
+          '--eval',
+          `
+          ${initialize || ''}
+          ${wrapperExpression}
+          `,
+        ]);
+
+        strictEqual(stderr, '');
+        strictEqual(stdout, '');
+        strictEqual(code, 0);
+        strictEqual(signal, null);
+      }
+    }
+  });
+
+  it('should crash when the expression is not valid', async () => {
+    let { code, signal, stdout, stderr } = await spawnPromisified(process.execPath, [
+      '--eval',
+      `
+      function callAwait() {}
+      callAwait(await "" ""); 
+      `,
+    ]);
+    match(stderr, /SyntaxError: missing \) after argument list/);
+    strictEqual(stdout, '');
+    strictEqual(code, 1);
+    strictEqual(signal, null);
+
+    ({ code, signal, stdout, stderr } = await spawnPromisified(process.execPath, [
+      '--eval',
+      `
+      function callAwait() {}
+      if (a "") {}
+      `,
+    ]));
+    match(stderr, /SyntaxError: Unexpected string/);
+    strictEqual(stdout, '');
+    strictEqual(code, 1);
+    strictEqual(signal, null);
+  });
+});